Chemical compound



Patented Oct. 9, 1945 CHEMICAL COMPOUND Joy G. Lichty, Stow, Ohio,assignor to Wingloot Ohio, a corporation of Corporation, Akron, DelawareNo Drawing. Application July 5, 1944, Serial No. 543,603

2 Claims.

This invention relates to a new ester of alpha chloroacrylic acidderived by dehydrochlorination of the 2,3-dichloro-n-propylalpha-beta-di chloropropionate. The new compound is known as2,3-dichloro-n-propyl. alpha-chloroacrylate and has the molecularstructure Although dehydrochlorinations of alpha, beta,dichloropropionic acid esters have been performed previously, thedichloropropyl ester has not been so treated. It would be expected thatthe dichloropropyl radical would also be dehydrochlorinated by the samereaction. I have discovered that 2,3-dichloropropylalpha chloroacrylatecan be prepared by heating 2,3-dichloropropyl alpha-betadichloropropionate in the presence of materials known to bedehydrochlorination catalysts, such as alumina, metal halides, alkalicarbonates, clay or carbon. I have found that surprisingly good resultscan be obtained by the use of amino compounds, particularly tertiaryamines. Accordingly, my preferred procedure involves the catalyticdehydrochlorination by heating at temperatures of 80 to 100 C. in thepresence of compounds, such as N,N-dimethyl aniline, tributyl amine,triamylamine, pyridine and quinoline. The dehydrochlorination ispreferably conducted in the presence of a polymerization inhibitor suchas hydroquinone, pyrogallol, phenyl-beta-naphthylamine andN,N'-dipheny1-parapheny1ene diamine to prevent the simultaneouspolymerization of the product.

The new compound is valuable as a monomer in the preparation ofsynthetic resins by polymerization. Such reactions may be masspolymerizations conducted by heating in the presence of organicperoxides, such as benzoyl peroxide, to form transparent colorlesssolids. Mass copolymers may be prepared by reacting a mixture of thedichloropropyl chloroacrylate and one or more other monomers such asvinyl acetate, methyl methacrylate and vinyl chloride. Solvents,plasticizers, pigments or reinforcing agents may be added to suit.

The polymerization may also be conducted in aqueous suspension using anemulsifying agent, such as sodium oleate and an oxidant, such as sodiumperborate. Such reactions which produce rubber-like polymers are usuallyinduced at temperatures between 30 and 80 C. The latex so obtained iscoagulated by methods known to the art and the polymer separated fromthe water and Water soluble impurities. Emulsion copolymers ofdichloropropyl alpha chloroacrylate and vinyl chloride, butadiene-1',3,styrene or vinylidene chloride may be prepared, preferably with lessthan 50% of the ester.

Further details of the preparation of the new chemical compound will beapparent in the following detailed description.

Equal molecular proportions of 2,3-dichloropropanol-l andalpha-beta-dichloropropionic acid were placed in a reaction flask withbenzene and 0.5% of toluene sulphonic acid (based on the combined weightof the reactants). The mixture was refluxed for 10 hours. The waterevolved during the reaction was condensed with the benzene and separatedtherefrom before the benzene was returned to the reaction vessel.

A mixture of 65.8 grams of the 2,3-dichloropropylalpha-beta-dichloropropionate prepared as above described, 34.5 grams ofdimethyl aniline and 6 grams of N,N'-diphenyl-para-phenylene diamine washeated on a steam bath at 90 C. for 1 hours. The resulting product waswashed with dilute hydrochloric acid and water and then distilled at 30mm. pressure. The fraction boiling between 133 and 143 C. was identilledas 2,3-dichloropropyl alpha-chloroacrylate having a density of 26 1 5 of1.384 and an index of refraction (N of 1.4920.

This application is a continuation-in-part of my application Serial No.449,187 filed June 30,

Although the invention has been described with respect to a specificprocedure, it is not intended that the details tions on the scope of theinvention, except as included in the following claims. I claim:

1. As a new compound, 2,3-dichloropropyl alpha-chloroacrylate.

2. A method of preparing 2,3-dichloropropyl alpha-chloroacrylate whichcomprises heating alpha-beta-dichloroproof tertiary amines;

JOY G. LICHTY.

2,3-dichloro-n-propyl .pionate in the presence thereof shall be limita-

